US4129593A - Process for the production of high purity S-carboxymethyl-L-cysteine - Google Patents
Process for the production of high purity S-carboxymethyl-L-cysteine Download PDFInfo
- Publication number
- US4129593A US4129593A US05/833,043 US83304377A US4129593A US 4129593 A US4129593 A US 4129593A US 83304377 A US83304377 A US 83304377A US 4129593 A US4129593 A US 4129593A
- Authority
- US
- United States
- Prior art keywords
- cysteine
- reducing agent
- acid
- sulfur
- disodium salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- GBFLZEXEOZUWRN-VKHMYHEASA-N S-carboxymethyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CSCC(O)=O GBFLZEXEOZUWRN-VKHMYHEASA-N 0.000 title 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims abstract description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 21
- GBFLZEXEOZUWRN-VKHMYHEASA-M S-carboxylatomethyl-L-cysteine(1-) Chemical compound [O-]C(=O)[C@@H]([NH3+])CSCC([O-])=O GBFLZEXEOZUWRN-VKHMYHEASA-M 0.000 claims abstract description 18
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229940106681 chloroacetic acid Drugs 0.000 claims abstract description 16
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 claims abstract description 15
- 229960003067 cystine Drugs 0.000 claims abstract description 15
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000004158 L-cystine Substances 0.000 claims abstract description 14
- 235000019393 L-cystine Nutrition 0.000 claims abstract description 14
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 13
- 239000004201 L-cysteine Substances 0.000 claims abstract description 11
- 235000013878 L-cysteine Nutrition 0.000 claims abstract description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 10
- 239000011734 sodium Substances 0.000 claims abstract description 10
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 10
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 8
- 239000007864 aqueous solution Substances 0.000 claims abstract description 8
- 239000011541 reaction mixture Substances 0.000 claims abstract description 4
- PWKSKIMOESPYIA-UHFFFAOYSA-N 2-acetamido-3-sulfanylpropanoic acid Chemical compound CC(=O)NC(CS)C(O)=O PWKSKIMOESPYIA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 230000001376 precipitating effect Effects 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 13
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 230000007717 exclusion Effects 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 230000008016 vaporization Effects 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 238000001704 evaporation Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical class OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- HEZHYQDYRPUXNJ-UHFFFAOYSA-L potassium dithionite Chemical compound [K+].[K+].[O-]S(=O)S([O-])=O HEZHYQDYRPUXNJ-UHFFFAOYSA-L 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- RWPGFSMJFRPDDP-UHFFFAOYSA-L potassium metabisulfite Chemical compound [K+].[K+].[O-]S(=O)S([O-])(=O)=O RWPGFSMJFRPDDP-UHFFFAOYSA-L 0.000 description 1
- 235000010263 potassium metabisulphite Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
Definitions
- the invention is directed to a process for the production of very pure S-carboxymethyl-L-cysteine by reacting L-cystine in liquid ammonia with metallic sodium to form the disodium salt of L-cysteine, vaporizing the ammonia, reacting the disodium salt of L-cysteine with an aqueous solution of chloracetic acid and precipitating the S-carboxymethyl-L-cysteine formed by acidifying the reaction mixture.
- SCC S-carboxymethyl-L-cysteine
- the process of the invention is characterized by the reaction of the disodium salt of L-cysteine with an aqueous solution of chloroacetic acid taking place in the presence of 0.1 to 10 weight percent, based on the chloroacetic acid of a reducing agent.
- the reducing agent is used in an amount of 1 to 5 weight percent based on the weight of chloroacetic acid employed.
- alkali salts of oxygen containing acids of sulfur at a lower stage of oxidation e.g., the corresponding dithionites, sulfoxylates or pyrosulfites and formic acid.
- alkali salts are sodium dithionite, potassium dithionite, sodium pyrosulfite and potassium pyrosulfite.
- sodium bisulfite and potassium bisulfite for example.
- the reaction of L-cystine in liquid ammonia with metallic sodium suitably takes place at a temperature from -60° to +20° C. Especially advantageous are temperatures from -5° to +10° C., on the one hand to save cold energy and on the other to avoid too high pressures.
- the ammonia is vaporized, suitably at normal pressure (i.e., atmospheric pressure) and can be recovered for renewed use.
- the disodium salt of L-cysteine remaining behind is taken up in water and reacted with an aqueous solution of chloroacetic acid which simultaneously contains the reducing agent.
- the reaction takes place suitably at a temperature of +20° to 100° C., preferably at a temperature of 30° to 50° C.
- the reaction generally requires a time of about one hour.
- To produce higher yields of SCC it is advantageous to use the chloroacetic acid in a molar excess of about 15 to 25%.
- the concentration of chloroacetic acid in water is not critical, but usually is between 100 and 600 grams/liter.
- reaction mixture is cooled to room temperature and is adjusted with a mineral acid, for example hydrochloric acid to a pH of about 2.5 to 3.0.
- a mineral acid for example hydrochloric acid
- suitable acids include hydrobromic acid and sulfuric acid.
- the process can comprise, consist essentially of or consist of the steps set forth using the recited materials.
- the aqueous solution of the disodium salt of L-cysteine obtained is then reacted at 20° to 30° C. under a nitrogen atmosphere in the course of 30 minutes with stirring with a solution of 104 grams of chloroacetic acid (1.1 moles) and 4 grams of sodium pyrosulfite in 200 ml of water. It is also allowed to post react for 15 minutes at 20° C., the solution clarified over activated carbon and the filtrate treated with 90 ml of concentrated hydrochloric acid to a pH of 2.5. Thereby the S-carboxymethyl-L-cysteine precipitates out in crystalline form. The product is filtered off with suction, well stirred in 500 ml of water, again filtered with suction and dried in a vacuum at 70° C.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2647094A DE2647094B1 (de) | 1976-10-19 | 1976-10-19 | Verfahren zur Herstellung von hochreinem S-Carboxymethyl-L-cystein |
| DE2647094 | 1976-10-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US4129593A true US4129593A (en) | 1978-12-12 |
Family
ID=5990806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/833,043 Expired - Lifetime US4129593A (en) | 1976-10-19 | 1977-09-14 | Process for the production of high purity S-carboxymethyl-L-cysteine |
Country Status (8)
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105418471A (zh) * | 2015-12-24 | 2016-03-23 | 宜昌三峡制药有限公司 | 一种羧甲司坦的合成方法 |
| CN106083673A (zh) * | 2016-06-29 | 2016-11-09 | 罗江晨明生物制品有限公司 | 一种羧甲司坦的制备工艺 |
| CN110563596A (zh) * | 2019-09-16 | 2019-12-13 | 山东泰和水处理科技股份有限公司 | 一种二羧甲基氨基酸盐的制备方法 |
| CN111138326A (zh) * | 2019-12-31 | 2020-05-12 | 宁波市远发生物工程有限公司 | 一种s-羧甲基-l-半胱氨酸的制备方法 |
| CN115557864A (zh) * | 2021-07-01 | 2023-01-03 | 广东众生药业股份有限公司 | 一种羧甲司坦的工业化制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2460785A (en) * | 1946-03-14 | 1949-02-01 | Merck & Co Inc | Processes for preparing substituted propanoic acid |
| US3184505A (en) * | 1962-06-18 | 1965-05-18 | Mead Johnson & Co | Process for the n-monoacylation of cysteine |
-
1976
- 1976-10-19 DE DE2647094A patent/DE2647094B1/de active Granted
-
1977
- 1977-08-15 NL NL7708981A patent/NL7708981A/xx not_active Application Discontinuation
- 1977-09-14 US US05/833,043 patent/US4129593A/en not_active Expired - Lifetime
- 1977-09-22 FR FR7728567A patent/FR2371423A1/fr active Granted
- 1977-10-14 GB GB42819/77A patent/GB1532940A/en not_active Expired
- 1977-10-18 BE BE6046183A patent/BE859870A/xx not_active IP Right Cessation
- 1977-10-18 CH CH1269777A patent/CH628618A5/de not_active IP Right Cessation
- 1977-10-18 JP JP12503777A patent/JPS5350118A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2460785A (en) * | 1946-03-14 | 1949-02-01 | Merck & Co Inc | Processes for preparing substituted propanoic acid |
| US3184505A (en) * | 1962-06-18 | 1965-05-18 | Mead Johnson & Co | Process for the n-monoacylation of cysteine |
Non-Patent Citations (4)
| Title |
|---|
| Berezovskii, V. M. et al. "Synthesis of Substituted 3-Ketothiophanes by Dieckmann Cyclization" J. Gen. Chem. U.S.S.R. (1963) pp. 2815-2820. * |
| Greenstein, Jessie P. et al. "Chemistry of the Amino Acids" vol. 3 (1961) p. 1901, Wiley Publ. * |
| Kirk-Othmer "Encyclopedia of Chemical Technology" 2nd Ed. vol. 10, pp. 100 and 102, Interscience Publ. * |
| Mellor, J. W. "Inorganic and Theoretical Chemistry", vol. 10 (1949) p. 171, Longmans, Green & Co. Publ. * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105418471A (zh) * | 2015-12-24 | 2016-03-23 | 宜昌三峡制药有限公司 | 一种羧甲司坦的合成方法 |
| CN105418471B (zh) * | 2015-12-24 | 2017-09-05 | 宜昌三峡制药有限公司 | 一种羧甲司坦的合成方法 |
| CN106083673A (zh) * | 2016-06-29 | 2016-11-09 | 罗江晨明生物制品有限公司 | 一种羧甲司坦的制备工艺 |
| CN106083673B (zh) * | 2016-06-29 | 2017-11-03 | 罗江晨明生物制品有限公司 | 一种羧甲司坦的制备工艺 |
| CN110563596A (zh) * | 2019-09-16 | 2019-12-13 | 山东泰和水处理科技股份有限公司 | 一种二羧甲基氨基酸盐的制备方法 |
| CN110563596B (zh) * | 2019-09-16 | 2022-07-26 | 山东泰和水处理科技股份有限公司 | 一种二羧甲基氨基酸盐的制备方法 |
| CN111138326A (zh) * | 2019-12-31 | 2020-05-12 | 宁波市远发生物工程有限公司 | 一种s-羧甲基-l-半胱氨酸的制备方法 |
| CN115557864A (zh) * | 2021-07-01 | 2023-01-03 | 广东众生药业股份有限公司 | 一种羧甲司坦的工业化制备方法 |
| CN115557864B (zh) * | 2021-07-01 | 2024-06-18 | 广东众生药业股份有限公司 | 一种羧甲司坦的工业化制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5350118A (en) | 1978-05-08 |
| FR2371423B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-08-29 |
| BE859870A (fr) | 1978-04-18 |
| FR2371423A1 (fr) | 1978-06-16 |
| JPS5542987B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-11-04 |
| NL7708981A (nl) | 1978-04-21 |
| DE2647094C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-02-08 |
| DE2647094B1 (de) | 1978-04-13 |
| CH628618A5 (de) | 1982-03-15 |
| GB1532940A (en) | 1978-11-22 |
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